Stereoselective intramolecular Diels-Alder reactions of 3-alkenyl(oxy)-2(1H)-pyrazinones

被引：13

作者：

De Borggraeve, WM ^{[1
]}

Rombouts, FJR ^{[1
]}

Verbist, BMP ^{[1
]}

Van der Eycken, EV ^{[1
]}

Hoornaert, GJ ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Synth Organ Lab, B-3001 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 03期

关键词：

pyrazinone; cycloaddition; Diels-Alder reaction; brevianamide;

D O I：

10.1016/S0040-4039(01)02188-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dichloropyrazinones are reacted with alkenolates or a Grignard reagent in order to tether a dienophilic side-chain at the 3-position. The compounds smoothly undergo intramolecular Diels -Alder reaction forming tricyclic ring systems. The reactions proceed completely stereoselective yielding only endo adducts. In the case of the alkenylpyrazinone, the core skeleton of the breviamides is obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：447 / 449

页数：3

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